Five-membered Alicyclic Ring Containing Patents (Class 568/838)
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Patent number: 4806694Abstract: Fluorine-containing polyols obtained by the free radical addition of a fluoro-olefin having the general formula: ##STR1## wherein Y represents F and Z represents Cl or F(CF.sub.2)n--wherein n is an integer from 0 to 10 or Y and Z together form a --(CF.sub.2)m-- chain wherein m represents an integer from 2 to 4 to a polyol wherein each hydroxyl group is directly attached to a group of the formula:--(CH.sub.2).sub.p O-- (2)wherein p is an integer of at least 4.Type: GrantFiled: September 10, 1987Date of Patent: February 21, 1989Assignee: Imperial Chemical Industries PLCInventors: Richard L. Powell, Brian Young
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Patent number: 4801759Abstract: A method for the continuous saponification of epoxides with 3-8 carbon atoms at low pressures, preferably atmospheric pressure, and low boiling temperatures with small amounts of water. Yields and selectivities are very high.Type: GrantFiled: August 7, 1987Date of Patent: January 31, 1989Assignee: Degussa AktiengesellschaftInventors: Rainer Siegmeier, Gu Prescher, Helmut Maurer
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Patent number: 4789685Abstract: 9-fluoroprostane derivatives of Formula I ##STR1## wherein R.sub.1 is CH.sub.2 OH or ##STR2## wherein R.sub.2 is hydrogen, alkyl, cycloalkyl, aryl, or a heterocyclic residue; or R.sub.1 is the residue ##STR3## wherein R.sub.3 is an acid residue or R.sub.2 and A is --CH.sub.2 --CH.sub.2 -- or cis--CH.dbd.CH--,B is --CH.sub.2 --CH.sub.2 --, trans--CH.dbd.CH-- or --C.tbd.C,W is a free or functionally modified hydroxymethylene group wherein the OH-group can be in the .alpha.- or .beta.- position,D and E jointly are a direct bond orD is straight-chain or branched alkylene or alkenylene of 1-10 carbon atoms which can optionally be substituted by fluorine atoms, and E is oxygen or sulfur, a direct bond, --C.tbd.C-- or --CR.sub.6 .dbd.CR.sub.7 -- wherein R.sub.6 and R.sub.7 differ from each other and each is hydrogen, chlorine, or alkyl,R.sub.4 is a free or functionally modified hydroxy group, andR.sub.5 is hydrogen, an optionally substituted aliphatic group, e.g.Type: GrantFiled: January 20, 1987Date of Patent: December 6, 1988Assignee: Schering AktiengesellschaftInventors: Werner Skuballa, Bernd Raduechel, Norbert Schwarz, Helmut Vorbrueggen, Walter Elger, Olaf Loge, Michael-Harold Town
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Patent number: 4783558Abstract: Flavoring and perfume compositions, flavored foodstuffs and luxury consumables and perfumed products which contain (+)-spathulenol and/or (+)-4a-allospathulenol, having respective structural formula ##STR1## as the base material, (+)-4a-allospathulenol per se and a process for the preparation of these spathulenols.Type: GrantFiled: April 10, 1987Date of Patent: November 8, 1988Assignee: Naarden International N.V.Inventors: Leendert M. van der Linde, Franciscus P. van Lier, Antonius J. A. van der Weerdt
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Patent number: 4766002Abstract: Compounds of the general formula ##STR1## wherein R is hydrogen or an acyl group of two to five carbon atoms and the dotted line is an optional bond, are valuable flavor compounds and can be used to improve the flavor of foodstuffs and luxury consumables.Type: GrantFiled: February 13, 1986Date of Patent: August 23, 1988Assignee: Givaudan CorporationInventors: Martin Rohr, Richard H. Potter, Richard E. Naipawer
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Patent number: 4719043Abstract: The invention relates to isomeric 1-alkyl/alkenyl-2,2,4(2,4,4)-trimethyl cyclopentan-1-ols corresponding to general formulae I a/b below ##STR1## in which R is C.sub.2-5 alkyl or a C.sub.3-5 alkenyl; the use of compounds of the same formula in which R is C.sub.1-5 alkyl or C.sub.2-5 alkenyl as perfumes in compositions containing active chlorine or capable of generating active chlorine; and methods for their preparation.Type: GrantFiled: March 20, 1987Date of Patent: January 12, 1988Assignee: Henkel Kommanditgesellschaft auf AktienInventors: Ulf-Armin Schaper, Klaus Bruns, Siegfried Bloesl, Benno Streschnak
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Patent number: 4701540Abstract: A process for producing cycloketones of a 5 or 6 carbon chain length through which said ketones are known intermediates for producing carotenoids.Type: GrantFiled: March 12, 1984Date of Patent: October 20, 1987Assignee: Hoffmann-La Roche Inc.Inventors: Teodor Lukac, Milan Soukup, Erich Widmer
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Patent number: 4696766Abstract: (2R*,3S*)-(E)-3-Methyl-5-(2,2,3-trimethylcyclopent-3-en-1-yl)pent-4-en-2-ol possesses a very intense creamy, woody, musk, sandalwood odor and is a valuable ingredient for use in fragrance compositions for its musk and sandalwood-like qualities. This odorant is more intense than any of the campholenic aldehyde derivatives that have been previously reported.Type: GrantFiled: March 19, 1986Date of Patent: September 29, 1987Assignee: Givaudan CorporationInventor: Richard E. Naipawer
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Patent number: 4693845Abstract: Novel bornane-3-spiro-1'-cylopentane derivatives of the following formula (I) ##STR1## in which R.sub.1 and R.sub.2 are defined such that when R.sub.1 is a hydrogen atom, R.sub.2 is a hydroxyl group, or R.sub.1 and R.sub.2 are joined to form a ketone are obtained from camphor.The derivatives are synthesized in a simple process from an economical starting material, camphor. The derivatives have woody-note and can be widely used in perfumes, soaps, shampoos, hair rinses, cosmetics and the like.Type: GrantFiled: June 18, 1986Date of Patent: September 15, 1987Assignee: KAO CorporationInventors: Yoshiaki Fujikura, Akira Yamamuro, Motoki Nakajima
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Patent number: 4691064Abstract: A method for producing cycloalkanols important as a material for caprolactam, adipic acid and the like, which comprises carrying out the catalytic hydration of a cycloalkene using as a catalyst an aromatic sulfonic acid having at least one hydroxyl or ether group and separating the resulting cycloalkanol from the reaction solution by extraction.Type: GrantFiled: November 12, 1986Date of Patent: September 1, 1987Assignee: Sumitomo Chemical Company, LimitedInventors: Tamio Shirafuji, Itaru Kawata
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Patent number: 4686310Abstract: Described are the 2-isopropenyl-5-methylcyclopentanealkanols and esters thereof having the generic structure: ##STR1## wherein R.sub.1 represents hydrogen or C.sub.2 -C.sub.3 acyl and wherein n represents 0 or 1 and uses thereof in augmenting or enhancing the aroma of consumable materials including perfume compositions, colognes and perfumed articles such as solid or liquid anionic, cationic, nonionic or zwitterionic detergents, perfumed polymers, cosmetic compositions, fabric softener compositions, fabric softener articles and hair preparations.Type: GrantFiled: May 29, 1986Date of Patent: August 11, 1987Assignee: International Flavors & Fragrances Inc.Inventor: John B. Hall
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Patent number: 4666629Abstract: Described is an economical and novel process for preparing a mixture containing 2-campholenylidenbutanol having the structure: ##STR1## by means of reacting the compound having the structure: ##STR2## with hydrogen in the presence of a copper chromite catalyst having the formula:CuO.CuCr.sub.2 O.sub.4as well as uses of such mixtures in augmenting or enhancing the aroma of perfume compositions, colognes and perfumed articles including fabric softener compositions, cosmetic powders and solid or liquid anionic, cationic, nonionic or zwitterionic detergents.Type: GrantFiled: August 8, 1986Date of Patent: May 19, 1987Assignee: International Flavors & Fragrances Inc.Inventors: Wilhelmus J. Wiegers, Mark A. Sprecker, William L. Schreiber
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Patent number: 4661641Abstract: Compounds of the formula ##STR1## wherein n is either 0 or 1; R.sup.1 and R.sup.2 is hydrogen and the other is hydrogen, hydroxy, oxo group, a protected hydroxy or protected oxo group; R.sup.3 is hydroxy oxo group, .dbd.CH--CH.sub.2 --OH, .dbd.CH--CHO or one of the foregoing groups where the hydroxy or oxo functions are protected; R.sup.4 is --CO--OR.sup.6, --CO--R.sup.6, --CO--NR.sup.6 R.sup.7, --CO--Cl or --SO.sub.2 --R.sup.6 ; R.sup.6 is saturated or aromatic hydrocarbon; and R.sup.7 is saturated or aromatic hydrocarbon or hydrogen,are converted by cleavage of R.sup.4 OH into corresponding cycloalkenes and protecting groups, if present, are hydrolyzed.The compounds obtained are valuable intermediates in carotenoid syntheses.Type: GrantFiled: May 29, 1984Date of Patent: April 28, 1987Assignee: Hoffmann-La Roche Inc.Inventors: Teodor Lukac, Milan Soukup, Erich Widmer
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Patent number: 4658056Abstract: A process for the catalytic oxidation of liquid cycloparaffins to oxidation products thereof is disclosed. In the process, partial oxidation products are formed by oxidizing the cycloparaffin with molecular oxygen-containing gas in the presence of an oxidation catalyst comprising two heavy metal compounds. The first heavy metal compound is a cobalt compound having ligands selected from dialkyl phosphate, dicycloalkylphosphate and alkylcycloalkylphosphate, optionally additionally combined with pyridine. The second heavy metal compound is a chromium alkanoate. A preferred catalyst is cobalt bis[di(2-ethylhexyl)phosphate] combined with chromium naphthenate.Type: GrantFiled: April 22, 1982Date of Patent: April 14, 1987Assignee: Du Pont Canada Inc.Inventor: Peter A. Sipos
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Patent number: 4640801Abstract: Graft polyols comprising the liquid reaction product of a vegetable oil or unsaturated fatty carbon compound having at least eight carbon atoms, at least one hydroxyl group, and at least one double bond, a cyclopentadienyl compound and a terminally unsaturated monomer having at least one hydroxyl group. These liquid low viscosity polyols when cured with a polyisocyanate, melamine, or formaldehyde compound yield high solids or solventless polyurenthane compositions useful as coatings, adhesives, potting or molding compounds.Type: GrantFiled: December 12, 1984Date of Patent: February 3, 1987Assignee: CasChem, Inc.Inventors: Dominic Simone, Melvin Brauer
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Patent number: 4627935Abstract: Described are the 2-isopropenyl-5-methylcyclopentanealkanols and esters thereof having the generic structure: ##STR1## wherein R.sub.1 represents hydrogen or C.sub.2 -C.sub.3 acyl and wherein n represents 0 or 1 and uses thereof in augmenting or enhancing the aroma of consumable materials including perfume compositions, colognes and perfumed articles such as solid or liquid anionic, cationic, nonionic or zwitterionic detergents, perfumed polymers, cosmetic compositions, fabric softener compositions, fabric softener articles and hair preparations.Type: GrantFiled: February 6, 1985Date of Patent: December 9, 1986Assignee: International Flavors & Fragrances Inc.Inventor: John B. Hall
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Patent number: 4626603Abstract: Aliphatic or cyclic epoxides containing 3 to 8 carbon atoms which are present in aromatic hydrocarbons or halohydrocarbons are saponified continuously and directly to vicinal diols without the use of high temperatures and pressures which would otherwise be necessary. The saponification is acid catalyzed.Type: GrantFiled: November 15, 1985Date of Patent: December 2, 1986Assignee: Degussa AktiengesellschaftInventors: Rainer Siegmeier, Gunter Prescher, Helmut Maurer
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Patent number: 4619781Abstract: Described is an economical and novel process for preparing a mixture containing 2-campholenylidenbutanol having the structure: ##STR1## by means of reacting the compound having the structure: ##STR2## with hydrogen in the presence of a copper chromite catalyst having the formula:CuO.CuCr.sub.2 O.sub.4as well as uses of such mixtures in augmenting or enhancing the aroma of perfume compositions, colognes and perfumed articles including fabric softener compositions, cosmetic powders and solid or liquid anionic, cationic, nonionic or zwitterionic detergents.Type: GrantFiled: September 20, 1985Date of Patent: October 28, 1986Assignee: International Flavors & Fragrances Inc.Inventors: Wilhelmus J. Wiegers, Mark A. Sprecker, William L. Schreiber
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Patent number: 4601850Abstract: Described are 1-hydroxymethyl-2-isopropenyl-1,5-dimethylcyclopentane and the n-propyl ester thereof defined according to the structure: ##STR1## wherein R represents hydrogen or n-propyl.Type: GrantFiled: December 21, 1984Date of Patent: July 22, 1986Assignee: International Flavors & Fragrances Inc.Inventor: Richard M. Boden
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Patent number: 4578396Abstract: Hydroxyalkinyl-azolyl derivatives of the formula ##STR1## in which A is a nitrogen atom or the CH group,R is optionally substituted alkyl, cycloalkyl or phenyl,R.sup.1 is hydrogen, alkyl, alkenyl, alkinyl, or optionally substituted benzyl,R.sup.2 is hydrogen or methyl, andX is hydrogen, bromine or iodine,or addition products thereof with acids or metal salts exhibit fungicidal activity. Some intermediates therefor are also new.Type: GrantFiled: May 27, 1983Date of Patent: March 25, 1986Assignee: Bayer AktiengesellschaftInventors: Gerhard Jager, Klaus Bockmann, Karl H. Buchel, Wilhelm Brandes, Paul-Ernst Frohberger, Hans Scheinpflug
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Patent number: 4571345Abstract: Compounds of the formula: ##STR1## wherein n is 0 or 1, R is lower alkyl (substituted or unsubstituted), R' is H or lower alkyl, and R" is a branched alkyl, alkyl-cycloalkyl, cycloalkyl, polycycloalkyl (poly=2 or more, fused or non-fused), phenyl or alkyl-substituted phenyl, and physiologically acceptable cationic and acid addition salts thereof, which compounds are potent sweeteners. These derivatives of gem-diaminoalkanes are many times sweeter than sugar and are free from undesirable flavor qualities. Furthermore, they possess an unanticipated high degree of solubility compared with known synthetic sweeteners. In addition, the compounds possess high stability so that they can be used in all types of beverages and in conventional food processing. Sweetening compositions and sweetened edible compositions of these compounds are also provided.Type: GrantFiled: June 13, 1983Date of Patent: February 18, 1986Assignee: Cumberland Packing Corp.Inventors: Michael S. Verlander, William D. Fuller, Murray Goodman
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Patent number: 4562299Abstract: A process for the preparation of water-soluble vicinal diols by means of a direct catalytic hydroxylation of the corresponding olefines with H.sub.2 O.sub.2. An olefine possibly carrying functional groups inert under the reaction conditions, and whose corresponding vicinal diol is soluble in water, is made to react, under vigorous stirring, with H.sub.2 O.sub.2 at a temperature between 0.degree. and 120.degree. C. and at a pressure between 1 and 100 atmospheres, in a two-phase aqueous liquid/organic liquid system consisting or consisting essentially of an acid aqueous phase containing H.sub.2 O.sub.2 and of an organic phase containing (1) said olefine; (2) possibly a solvent immiscible with the aqueous phase; and (3) a catalyst of the formula:Q.sub.3 XW.sub.4 O.sub.24-2nwherein Q represents an onium (RR.sub.1 R.sub.2 R.sub.3 M).sup.+ cation, wherein M is chosen from among N, P, As and Sb, and R, R.sub.1, R.sub.2 and R.sub.Type: GrantFiled: December 12, 1984Date of Patent: December 31, 1985Assignee: Montedison S.p.A.Inventors: Carlo Venturello, Mario Gambaro
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Patent number: 4533772Abstract: The process for hydroxylating olefins with oxygen in the presence of water, an osmium-halide (e.g., OsBr.sub.3) catalyst and transition metal containing co-catalyst (CuBr.sub.2) is disclosed.Type: GrantFiled: August 29, 1983Date of Patent: August 6, 1985Assignee: Exxon Research & Engineering Co.Inventors: Robert C. Michaelson, Richard G. Austin
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Patent number: 4533773Abstract: A process for hydroxylating olefins, such as ethylene or propylene, using an osmium oxide catalyst such as OsO.sub.4, a carboxylate salt co-catalyst, such as sodium acetate, and organic hydroperoxide oxidant is disclosed.Type: GrantFiled: March 22, 1984Date of Patent: August 6, 1985Assignee: Exxon Research & Engineering Co.Inventors: Robert C. Michaelson, Richard G. Austin
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Patent number: 4507512Abstract: An improved process for producing an alcohol by hydrating an olefin wherein the improvement comprises hydrating an olefin in the presence of a hydrogen-type catalyst having a silica/alumina molar ratio of 20 to 500 and a solvent using either:A. hydrogen-type mordenite or hydrogen-type zeolite Y, and a sulfone; orB. hydrogen-type crystalline aluminosilicate in which the entrance of the main void is formed by a 10-membered or 12-membered oxygen ring, and a C.sub.2 to C.sub.5 oxy acid or the lactones, lactides, methyl or ethyl esters thereof.Type: GrantFiled: May 14, 1984Date of Patent: March 26, 1985Assignee: Toa Nenryo Kogyo Kabushiki KaishaInventors: Yoshiharu Okumura, Setsuo Kamiyama, Hiroshi Furukawa, Katsumi Kaneko
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Patent number: 4501687Abstract: Novel cyclopentanols of the formula ##STR1## wherein R.sub.1 and R.sub.2 are identical and are selected from the group consisting of hydrogen and alkyl of 1 to 4 carbon atoms, R.sub.3 is selected from the group consisting of --OH, alkoxy of 1 to 8 carbon atoms and acyloxy of an organic carboxylic acid of 1 to 18 carbon atoms, R.sub.4 is selected from the group consisting of hydrogen and alkyl of 1 to 8 carbon atoms, R.sub.5 and R.sub.8 are individually selected from the group consisting of hydrogen, alkyl of 1 to 8 carbon atoms and alkenyl and alkynyl of 2 to 8 carbon atoms and R.sub.6 and R.sub.7 are individually selected from the group consisting of hydrogen, alkyl of 1 to 8 carbon atoms, alkenyl and alkynyl of 2 to 8 carbon atoms, --CN, --COCH.sub.3 and --COOAlK.sub.2 and AlK.sub.2 is alkyl of 1 to 8 carbon atoms useful as perfumery agents and their preparation and novel intermediates.Type: GrantFiled: November 30, 1981Date of Patent: February 26, 1985Assignee: Roussel UclafInventors: Jacques Martel, Jean Buendia, Francois Nezot
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Patent number: 4499313Abstract: An improved process for producing an alcohol by hydrating an olefin, wherein the improvement comprises hydrating an olefin in the presence of hydrogen-type mordenite or hydrogen-type zeolite Y as a catalyst each having a silica/alumina molar ratio of 20 to 500.Type: GrantFiled: April 30, 1984Date of Patent: February 12, 1985Assignee: Toa Nenryo Kogyo Kabushiki KaishaInventors: Yoshiharu Okumura, Setsuo Kamiyama, Toshihiro Hosokawa, Katsumi Kaneko
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Patent number: 4496777Abstract: Production of halohydrins; in particular, chlorohydrins by reaction of tertiary alkyl hypohalite and olefinically unsaturated compound in the presence of water and a water soluble salt of an amphoteric metal; in particular, a salt of tin, aluminum, zinc, zirconium, magnesium, or titanium, which provides a pH of from 2 to 5 under reaction conditions.Type: GrantFiled: November 9, 1983Date of Patent: January 29, 1985Assignee: The Lummus CompanyInventors: George D. Suciu, Joon T. Kwon, Atef M. Shaban
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Patent number: 4496778Abstract: A process directed to the hydroxylation of olefins by reacting said olefins in the presence of oxygen, water, and a catalyst composition comprising (i) a catalytically active osmium containing compound, (ii) a Co-catalyst I comprising a copper containing compound such as CuBr.sub.2, and (iii) a Co-catalyst II capable of increasing the rate and/or selectivity of the hydroxylation reaction, such as pyridine is disclosed.Type: GrantFiled: October 3, 1983Date of Patent: January 29, 1985Assignee: Exxon Research & Engineering Co.Inventors: Richard S. Myers, Robert C. Michaelson, Richard G. Austin
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Patent number: 4496779Abstract: A process directed to the hydroxylation of olefins by reacting said olefins in the presence of oxygen, water, and a catalyst composition comprising (i) a catalytically active osmium containing compound, (ii) a Co-catalyst I comprising a copper containing compound such as CuBr.sub.2, and (iii) a Co-catalyst II capable of increasing the rate and/or selectivity of the hydroxylation reaction, such as 1,4-diazabicyclo [2.2.2.] octane is disclosed.Type: GrantFiled: April 26, 1984Date of Patent: January 29, 1985Assignee: Exxon Research & Engineering Co.Inventors: Richard S. Myers, Robert C. Michaelson, Richard G. Austin
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Patent number: 4482763Abstract: A process for hydroxylating olefins with an organic hydroperoxide and water in the presence of an osmium containing catalyst (e.g. OsO.sub.4) and an organic halogenated hydrocarbon co-catalyst (e.g., n-butyl iodide) is disclosed.Type: GrantFiled: July 19, 1982Date of Patent: November 13, 1984Assignee: Exxon Research & Engineering Co.Inventors: Richard G. Austin, Robert C. Michaelson
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Patent number: 4479020Abstract: Production of halohydrins; in particular, chlorohydrins by reaction of tertiary alkyl hypohalite and olefinically unsaturated compound in the presence of water and a metal selected from Group II-A, II-B, III-A, III-B, IV-A, IV-B, or V-A of the Periodic Table. The use of such metals improves the production of halohydrin.Type: GrantFiled: November 12, 1982Date of Patent: October 23, 1984Assignee: The Lummus CompanyInventors: George D. Suciu, Joon T. Kwon, Atef M. Shaban
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Patent number: 4463194Abstract: A process for making piperitone from crude plinols involving hydrogenating the crude plinols to form dihydroplinols and dehydrating the dihydroplinols to yield an iridene. The iridene is then oxidatively cleaved at the unsaturation to form an acyclic dione. The dione is cyclized in the presence of a base to form piperitone.Type: GrantFiled: November 29, 1982Date of Patent: July 31, 1984Assignee: SCM CorporationInventor: Tse-Lok Ho
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Patent number: 4438287Abstract: Alcohols may be prepared in a combination process by subjecting an aliphatic paraffinic hydrocarbon feed stream to a dehydrogenation reaction and thereafter subjecting the reaction product mix comprising a mixture of aliphatic paraffinic hydrocarbons and aliphatic olefinic hydrocarbons, without separating the olefins in the product mix from the paraffins, to a hydroformylation reaction. The hydroformylation reaction is effected by treating said product mix with carbon monoxide and hydrogen in the presence of a catalyst comprising a rhodium-containing compound and a promoter comprising a trialkyl-substituted monoamine, all three of said alkyl moieties being substituted to the nitrogen of said amine to selectively prepare the desired alcohols.Type: GrantFiled: August 25, 1982Date of Patent: March 20, 1984Assignee: UOP Inc.Inventor: Tamotsu Imai
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Patent number: 4413151Abstract: A process for hydroxylating olefins using a supported osmium catalyst such as Os.sub.3 (CO).sub.12 adsorbed on a support, such as MgO, and optionally in conjunction with a co-catalyst such as NaI, is disclosed.Type: GrantFiled: July 14, 1982Date of Patent: November 1, 1983Assignee: Exxon Research & Engineering Co.Inventors: Robert C. Michaelson, Richard G. Austin, Donald A. White
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Patent number: 4401823Abstract: Polyhydroxylated compounds such as glucose, sucrose, sorbitol, etc. are subjected to a hydrogenolysis reaction at hydrogenolysis conditions which include a temperature in the range of from about 175.degree. to about 250.degree. C. and a pressure in the range of from about 10 to about 2000 pounds per square inch in the presence of a catalytic composition of matter. The catalyst comprises a carbonaceous pyropolymer possessing recurring units containing at least carbon and hydrogen atoms which is impregnated with a transition metal. The products which are obtained will include alcohols, acids, ketones, ethers, and hydrocarbons.Type: GrantFiled: May 18, 1981Date of Patent: August 30, 1983Assignee: UOP Inc.Inventor: Blaise J. Arena
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Patent number: 4393251Abstract: Hydrogenation catalysts which are prepared from mixed crystals of copper-zinc compounds, obtained by precipitation, of the formulaCu.sub.1.5-3 Zn.sub.1-2.5 (CO.sub.3).sub.1-2 (OH).sub.4-6.(H.sub.2 O).sub.0-1by decomposition at 200.degree.-500.degree. C., and are used for the catalytic preparation of propanediols of the formula ##STR1## where the R's may be identical or different and each is an aliphatic, araliphatic or aromatic radical, or the two R's together with the adjacent carbon atom are members of an alicyclic ring, by hydrogenating hydroxypropionaldehydes of the formula ##STR2## where R has the above meanings, and to processes for the preparation of propanediols, using such catalysts. The propane-1,3-diols obtainable by the novel process are valuable starting materials for the preparation of lubricants, plastics, surface coatings and synthetic resins, for example of polyesters derived from the propanediols.Type: GrantFiled: February 10, 1982Date of Patent: July 12, 1983Assignee: BASF AktiengesellschaftInventors: Franz J. Broecker, Leopold Hupfer, Franz Merger, Ernest Miesen, Juergen Paetsch, Guenter Zirker
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Patent number: 4390739Abstract: A process directed to the hydroxylation of olefins by reacting said olefins with an oxygen containing gas and water in the presence of a catalyst composition comprising (i) a catalytically active metal oxide such as OsO.sub.4, (ii) as a co-catalyst I a transition metal salt such as CuBr.sub.2, and (iii) optionally a co-catalyst II salt such as tetra ethyl ammonium bromide is disclosed.Type: GrantFiled: October 9, 1981Date of Patent: June 28, 1983Assignee: Exxon Research & Engineering Co.Inventors: Robert C. Michaelson, Richard G. Austin
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Patent number: 4386219Abstract: Hydrogenation catalysts, which have a specific surface area of from 50 to 150 square meters per gram, solely or partially contain crystals having a spinel structure and copper in the form of copper oxide, and have been obtained by precipitating copper and aluminum in a ratio of from 0.25 to 3 atoms of copper per atom of aluminum from their compounds in the presence of a carbonate at a pH of from 4.5 to 9 and calcining the resulting precipitate at from 300.degree. to 800.degree. C., for the catalytic preparation of propanediols by hydrogenating hydroxypropionaldehydes at not more than 300 bar pressure and from 50.degree. to 200.degree. C., and processes for the preparation of propanediols by the use of such catalysts.The propanediols obtainable by the process of the invention, in particular 2,2-dimethylpropane-1,3-diol, are valuable starting materials for the preparation of lubricants, plastics, surface coatings and synthetic resins, for example corresponding polyesters.Type: GrantFiled: February 2, 1982Date of Patent: May 31, 1983Assignee: BASF AktiengesellschaftInventors: Franz Merger, Ernest Miesen, Franz J. Broecker, Wolfgang Schroeder, Karl Baer, Juergen Paetsch, Leopold Hupfer
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Patent number: 4385185Abstract: Compounds of the general formula I: ##STR1## wherein R.sub.1 and R.sub.2 are equal or different alkyl-, alkoxyalkyl-, or aryl groups, or together form a ring; R.sub.3 is an allyl or benzyl radical; and R.sub.4 and R.sub.5 represent hydrogen, alkyl, alkoxyalkyl, alkenyl or further compounds of the formula II: ##STR2## wherein R.sub.1, R.sub.2, R.sub.4 and R.sub.5 have the meaning indicated above and R.sub.6 stands for hydrogen or methyl or to compounds which are modified by the addition of hydrogen to at least one olefinic or carbonylic double bond of compounds of the general formula I or II. The invention also relates to a process for preparing the new compounds. The compounds of the general formula II are obtained by thermal treatment of a selection of compounds of formula I, for which R.sub.3 stands for the allyl or methallyl radical. The compounds according to the invention are used as fragrant and flavoring substances.Type: GrantFiled: March 20, 1981Date of Patent: May 24, 1983Assignee: Consortium fur Elektrochemische Industrie GmbHInventors: Helmut Gebauer, Walter Hafner
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Patent number: 4338290Abstract: Glycols are readily and conveniently prepared by hydrolysis of halohydrins and/or dihaloalkanes in the presence of a catalytically effective amount of a strong acid.Type: GrantFiled: June 16, 1980Date of Patent: July 6, 1982Assignee: National Distillers & Chemical Corp.Inventors: Jawad H. Murib, John M. Inskeep
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Patent number: 4329508Abstract: A process for making mixed 2- and 3-C.sub.1 -C.sub.10 alkyl-2-cyclopenten-1-ones from a corresponding alkylcyclopentadiene by epoxidation to the oxiranes, hydrolysis to the diols, dehydration of the diols and rearrangement of the resulting mixed alkylcyclopentenones. The resulting product can be used to make methylcyclopentenolone, a synthetic maple flavor.Type: GrantFiled: September 29, 1980Date of Patent: May 11, 1982Assignee: SCM CorporationInventors: T. L. Ho, Shing-Hou Liu
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Patent number: 4327230Abstract: A process for the continuous production of an alkali metal alcoholate of a higher alcohol which comprises continuously introducing a higher alcohol into a reaction vessel, continuously introducing an alkali metal alcoholate of a lower alcohol into said reaction vessel and continuously and simultaneously distilling over and removing from said reaction vessel lower alcohol which forms.Type: GrantFiled: March 10, 1980Date of Patent: April 27, 1982Assignee: Dynamit Nobel AGInventors: Otto Ackermann, Hans Leuck, Gunther Meyer, Gerhard Schmeling
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Patent number: 4324730Abstract: Prostaglandin and prostacyclin compounds which are fluorine substituted in any one or more of the following positions, 4,4; 7,7; 10,10; and 5.Type: GrantFiled: October 8, 1980Date of Patent: April 13, 1982Assignee: The University of ChicagoInventor: Josef Fried
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Patent number: 4318831Abstract: Polyunsaturated cyclopentane derivatives of the general formula ##STR1## wherein R.sup.1 signifies a lower alkyl group with 1 to 3 carbon atoms and R.sup.2 signifies a hydroxymethyl, acetomethyl, or formyl group, and the wavy line on carbon atom 1 signifies epimeric forms have excellent aromatic properties and may be used in perfume compositions. The compounds in which R.sup.2 is hydroxymethyl have a pronounced sandalwood scent. Methods of production are also disclosed.Type: GrantFiled: June 15, 1979Date of Patent: March 9, 1982Assignee: Dragoco Gerberding & Co GmbHInventors: Erich Klein, Ernst J. Brunke
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Patent number: 4317941Abstract: The present specification relates to novel 9-deoxy-9-methylene-trans-2,3-didehydro-PGF compounds with improved pharmacological properties. While these compounds are useful in inducing a wide variety of prostaglandin-like pharmacological effects, they are specifically useful as regulators of procreation and fertility.Type: GrantFiled: August 11, 1978Date of Patent: March 2, 1982Assignee: The Upjohn CompanyInventor: Gordon L. Bundy
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Patent number: 4310700Abstract: Prostaglandin analogs are disclosed that have the .alpha.-chain terminating with the group --CH(OR')OR" wherein R' and R" are the same or different and are hydrogen, C.sub.1 to C.sub.4 alkanoyl or optionally substituted benzoyl, the substituents selected from the group C.sub.1 to C.sub.4 alkyl, C.sub.1 to C.sub.4 alkoxy, halo and trifluoromethyl. These compounds are useful as hypotensive agents, gastric secretory and platelet aggregation enhibitors and bronchodilators.Type: GrantFiled: April 3, 1980Date of Patent: January 12, 1982Assignee: American Cyanamid CompanyInventors: Allan Wissner, Middleton B. Floyd, Jr.
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Patent number: 4310709Abstract: The process for the manufacture of but-2-en-1-ol compounds by isomerizing but-3-en-1-ol compounds in the presence of a palladium catalyst and of hydrogen is improved by modifying the palladium catalyst with selenium or tellurium.The but-2-en-1-ols manufactured according to the invention are either solvents or valuable starting materials for the manufacture of solvents, dyes, surface coatings, paints and pesticides.Type: GrantFiled: April 23, 1980Date of Patent: January 12, 1982Assignee: BASF AktiengesellschaftInventor: Walter Rebafka
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Patent number: 4304733Abstract: Novel alcohols of the formula ##STR1## wherein R.sub.1 and R.sub.2 are individually selected from the group consisting of carbamoyl and R.sub.1 ' and R.sub.2 ', R.sub.1 ' and R.sub.2 ' are individually selected from the group consisting of hydrogen, halogen, alkyl of 1 to 6 carbon atoms, aryl of 6 to 10 carbon atoms, arylalkyl of 7 to 13 carbon atoms, alkoxycarbonyl of 2 to 5 carbon atoms and --CN and R.sub.3 and R.sub.3 ' are individually selected from the group consisting of hydrogen, alkyl of 1 to 3 carbon atoms and alkenyl of 2 to 3 carbon atoms in the S form, R form or racemic mixtures thereof whose esters with cyclopropane carboxylic acids have an elevated insecticidal activity and their preparation.Type: GrantFiled: April 17, 1980Date of Patent: December 8, 1981Assignee: Roussel UclafInventors: Jacques Martel, Jean Tessier, Andre Teche
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Patent number: 4298750Abstract: The novel borane-1,4-thioxane is synthesized by adding the calculated quantity of diborane to 1,4-thioxane. It is a stable liquid at 25.degree. C. The neat liquid is approximately 8.0 M in borane. The product, in spite of the additional oxygen atom in the ring, exhibits the desirable hydroborating and reducing action of borane-methyl sulfide. However, it possesses a major advantage over the latter in that the donor component, 1,4-thioxane, in contrast to methyl sulfide, is readily soluble in water and can be washed out of typical reaction mixtures. This greatly facilitates the synthetic applications of borane-1,4-thioxane over borane-methyl sulfide.Type: GrantFiled: February 19, 1980Date of Patent: November 3, 1981Assignee: Aldrich-Boranes, Inc.Inventor: Herbert C. Brown